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$165+ Cheap flights from Midland (MAF) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated November 6, 2025.

Round-trip from

$342
(Southwest)

One-way from

$165
(United Airlines)

Popular in

July

Cheapest in

April

Average price

$603
From Midland Intl to Caribbean
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One-way flight from Midland Intl to Caribbean
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Highest demand for flights based on searches. 3% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Midland to Caribbean

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/911:00 amMAF - SJU
2 stops8h 30mSouthwest
Fri 12/125:40 amSJU - MAF
2 stops12h 50mSouthwest
Deal found 11/4$342
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:30 amMAF - SJU
2 stops12h 52mUnited Airlines
Fri 12/127:45 amSJU - MAF
1 stop8h 12mUnited Airlines
Deal found 11/5$417
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:54 pmMAF - SJU
2 stops13h 15mAmerican Airlines
Fri 12/126:42 pmSJU - MAF
2 stops15h 56mAmerican Airlines
Deal found 11/5$420
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:00 amMAF - MBJ
1 stop6h 05mUnited Airlines
Sun 12/283:20 pmMBJ - MAF
1 stop18h 36mUnited Airlines
Deal found 11/5$618
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:00 pmMAF - MBJ
2 stops18h 30mUnited Airlines
Fri 11/141:25 pmMBJ - MAF
2 stops22h 59mUnited Airlines
Deal found 11/5$814
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/208:28 pmMAF - SDQ
2 stops17h 21mAmerican Airlines
Sat 1/106:00 amSDQ - MAF
2 stops18h 54mAmerican Airlines
Deal found 11/4$1,044
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/259:39 amMAF - SJU
1 stop9h 47mUnited Airlines
Sat 11/292:05 amSJU - MAF
2 stops21h 37mUnited Airlines
Deal found 11/6$1,335
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:00 amMAF - SJU
1 stop14h 26mUnited Airlines
Sun 1/47:45 amSJU - MAF
1 stop12h 34mUnited Airlines
Deal found 11/6$1,625
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/256:05 amMAF - SJU
2 stops9h 47mAmerican Airlines
Sun 11/306:00 amSJU - MAF
2 stops9h 54mAmerican Airlines
Deal found 11/6$1,693
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:00 amMAF - MBJ
2 stops8h 12mAmerican Airlines
Fri 11/1411:12 amMBJ - MAF
3 stops12h 41mAmerican Airlines
Deal found 11/5$1,725
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:00 amMAF - SJU
1 stop14h 26mUnited Airlines
Sun 1/47:45 amSJU - MAF
1 stop12h 34mUnited Airlines
Deal found 11/6$1,775
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:28 pmMAF - SJU
1 stop16h 31mAmerican Airlines
Sat 1/31:30 amSJU - MAF
1 stop12h 21mAmerican Airlines
Deal found 11/6$1,795

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 6, 2025.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 12/9

7:30 am-10:22 pm

2 stops12h 52m

San Juan Luis Munoz Marin Intl

Fri 12/12

7:45 am-1:57 pm

1 stop8h 12m

$417

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 12/9

6:54 pm-10:09 am

2 stops13h 15m

San Juan Luis Munoz Marin Intl

Fri 12/12

6:42 pm-8:38 am

2 stops15h 56m

$420

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 3/17

7:02 am-1:05 pm

1 stop6h 03m

Montego Bay Sangster Intl

Wed 3/25

2:20 pm-11:30 pm

1 stop9h 10m

$541

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 3/17

6:43 pm-10:55 am

2 stops16h 12m

Montego Bay Sangster Intl

Wed 3/25

10:50 am-10:28 pm

2 stops11h 38m

$546

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 3/10

7:20 am-5:25 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-1:39 pm

2 stops13h 34m

$552

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Mon 3/16

8:33 pm-1:00 pm

2 stops16h 27m

Montego Bay Sangster Intl

Tue 3/24

2:45 pm-8:45 am

2 stops18h 00m

$584

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sun 12/21

7:00 am-2:05 pm

1 stop6h 05m

Montego Bay Sangster Intl

Sun 12/28

3:20 pm-8:56 am

1 stop18h 36m

$618

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Mon 3/16

5:00 am-1:05 pm

1 stop8h 05m

Montego Bay Sangster Intl

Tue 3/24

2:20 pm-9:41 pm

1 stop7h 21m

$623

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 3/10

5:59 am-1:44 pm

1 stop7h 45m

Montego Bay Sangster Intl

Wed 3/11

2:45 pm-8:45 am

2 stops18h 00m

$656

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 3/10

5:00 am-1:05 pm

1 stop8h 05m

Montego Bay Sangster Intl

Wed 3/11

2:20 pm-4:24 pm

1 stop26h 04m

$661

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 23 results
1
2
3

Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean

What is the cheapest month to book a flight from Midland to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MAF to CB?

Find hourly flight availability from Midland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 6, 2025.

It’s typically best to fly out from Midland to Caribbean in the evening. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated November 6, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

  • How long is the flight from Midland to Caribbean?

    Airlines like United Airlines and American Airlines fly from Midland to Caribbean in about 12h 52m. The time it takes to get you to your destination can typically vary by up to 23m. The distance from Midland to Caribbean is about 2432 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Midland to Caribbean one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $165. However, be on the lookout for offers from American Airlines and Southwest, as they are both options that can get you from Midland to Caribbean for a low price.

  • What are the most popular routes from Midland to Caribbean?

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Montego Bay Sangster Intl and Midland Intl - Santo Domingo Las Americas.

  • Can I find deals for flights from Midland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean.

  • Can I find deals for business class flights from Midland to Caribbean?

    Yes. Cheapflights offers flight deals from Midland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midland to Caribbean

Discover the top 3 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$370Average$544FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$380Average$915FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$513Average$544FlexibilityNo cancel feeOn-time63%

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